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Chemistry 30A3 Fall 2011 Labs Dr. Troendle 27

Chemistry 30A3 Fall 2011 Labs Dr. Troendle 27 - φ C O C O...

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Chemical Biology 3OA3, September 2009 Page 27 Questions 1. 1-Benzylnicotinamide chloride can be prepared by heating nicotinamide with benzyl chloride in DMSO. Give a mechanism for the reaction and explain why alkylation occurs at the pyridine nitrogen. Why is DMSO a good solvent for this reaction? 2. 1-Benzylnicotinamide is similar to a naturally occuring enzyme cofactor that is used reduction/oxidation reactions. What is the name and structure? 3. Ethyl benzoylformate is not reduced by 1-benzyldihydronicotinamide alone. In the presence of magnesium chloride, however, racemic ethyl mandelate is formed in quantitative yield. Explain how MgCl 2 accelerates the reaction.
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Unformatted text preview: φ C O C O O Et φ CH HO C O O Et 1-benzyl dihydronicotinamide MgCl 2 ethyl benzoyl formate ethyl mandelate 4. When ethyl benzoylformate is treated with (R)-N-( α-methylbenzyl)-dihydronicotinamide in the presence of an equimolar amount of magnesium chloride in aqueous acetonitrile solution, the ethyl mandelate produced is 60% R and 40% S. a. Draw formulae indicating the structure and configuration of (R)-N-( α-methylbenzyl)-dihydronicotinamide and of the two enantiomers of ethyl mandelate. b. Explain why the product is not a racemic mixture. c. What is the enantiomeric excess of the ethyl mandelate? N NH O H H N-(α-methylbenzyl)-dihydronicotinamide...
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